89882-57-5

Upstream product

• 591-51-5 phenyllithium 
• 89882-56-4 5-chloro-4,4-diphenyl-2-t-butylisothiazolidin-3-one 
• 79250-34-3 5-bromo-2-t-butyl-4,4-diphenylisothiazolidin-3-one 
• 89882-59-7 3-chloro-2,2-diphenyl-3-phenylthio-N-t-buthylpropionamide 
• 89882-58-6 2,2-diphenyl-3-phenylthio-N-t-buthylpropionamide 
• 79250-30-9 4,4-diphenyl-2-t-butylisothiazolidin-3-one 
• 53216-38-9 2,2 diphenyl-3-mercapto-propionic acid 
• 97759-71-2 2,2-diphenyl-3-phenylsulfanyl-propionic acid 
• 79250-28-5 2,2,2',2'-tetyraphenyl-3,3'-dithiodipropionic acid 
• 79250-29-6 N,N'-di-t-butyl-2,2,2',2'-tetraphenyl-3,3'-dithiodipropionamide 

Relevant academic research and scientific papers

SYNTHESES OF β-LACTAMS BY RING CONTRACTION OF ISOTHIAZOLIDINONES

Several methods have been developed for the preparation of β-lactams from isothiazolidinones.Oxidation of 2-t-butyl-4,4-diphenyl- and 2,4,4-trimethyl-isothiazolidin-3-ones (4a) and (4b) with sulphuryl chloride afforded the 5-chloroisothiazolidinones (5a) and (5b), which were converted into 1-t-butyl-3,3-diphenyl- nd 1,3,3-trimethyl-4-phenylthioazetidin-2-ones (6a) and (6b) by treatment with phenyl-lithium.Alternatively, reaction of the isothiazolidinones (4a) and (4b) with phenyl-lithium gave N-t-butyl-2,2-diphenyl- and N,2,2-trimethyl-3-phenylthiopropionamides(12a) and (12b), which were transformed into the β-lactams (6a) and (6b) by halogenation at C-3, followed by treatment with potassium amide.These are examples of methods used to prepare β-lactams from isothiazolidinones.The verstility of these reactions and their relevance to penicilin biosynthesis is discussed.

Rearrangement of an Isothiazolidinone to a β-Lactam. A Model for Penicillin Biosynthesis

Based on novel syntheses of a β-lactam from an isothiazolidinone, a mechanism of formation of the β-lactam ring in penicillin biosynthesis is proposed.